scholarly journals Metal-Free Synthesis of Biaryl- and Teraryl-Cored Diarylmethanes by Ring Transformation of 2H-Pyran-2-ones

Synthesis ◽  
2018 ◽  
Vol 51 (06) ◽  
pp. 1435-1444 ◽  
Author(s):  
Fateh Singh ◽  
Priyanka Kole
Keyword(s):  
Reaction Products ◽  
Ring Transformation ◽  
Reaction Conditions ◽  
Metal Free ◽  
High Yields

An efficient metal-free approach for the synthesis of functionalized biaryl-cored diarylmethanes is described by the ring transformation of 2H-pyran-2-ones using 4-phenylbutan-2-one as carbanion source. Moreover, 2H-pyran-2-ones were reacted with 1,3-diphenylacetone in the presence of base to achieve functionalized teraryl-cored diarylmethanes. All the ring transformation reactions were performed under mild reaction conditions to afford the biaryl- and teraryl-cored reaction products in high yields.

Metal-free Synthesis of N-Sulfonylformamidines via Skeletal Reconstruction of Sulfonyl Oximonitriles

2022 ◽  
Author(s):  
Feng Li ◽  
Ziyan Wu ◽  
Jingjing Wang ◽  
Siyuan Zhang ◽  
Jiaxin Yu ◽  
...  
Keyword(s):  
Secondary Amines ◽  
Domino Reaction ◽  
Reaction Conditions ◽  
Metal Free ◽  
High Yields ◽  
Skeletal Reconstruction

We firstly develop an unprecedented domino reaction of sulfonyl oximonitriles with secondary amines to streamline synthesis of N-sulfonylformamidines in decent to high yields under mild reaction conditions. In addition, the...

scholarly journals Efficient Flow Electrochemical Alkoxylation of Pyrrolidine-1-carbaldehyde

Synlett ◽  
2019 ◽  
Vol 30 (10) ◽  
pp. 1183-1186 ◽  
Author(s):  
Nasser Amri ◽  
Ryan A. Skilton ◽  
Duncan Guthrie ◽  
Thomas Wirth
Keyword(s):  
Reaction Products ◽  
Reaction Conditions ◽  
Precise Control ◽  
High Yields ◽  
Electrochemical Microreactor

We report on the optimization of the alkoxylation of pyrrolidine-1-carbaldehyde by using a new electrochemical microreactor. Precise control of the reaction conditions permits the synthesis of either mono- or dialkoxylated reaction products in high yields.

scholarly journals Design, Synthesis, and In Vitro Evaluation of Benzofuro[3,2-c]Quinoline Derivatives as Potential Antileukemia Agents

Molecules ◽  
2020 ◽  
Vol 25 (1) ◽  
pp. 203 ◽  
Author(s):  
Ying Lin ◽  
Dong Xing ◽  
Wen-Biao Wu ◽  
Gao-Ya Xu ◽  
Li-Fang Yu ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Biological Evaluation ◽  
Quinoline Derivatives ◽  
Reaction Conditions ◽  
Design Synthesis ◽  
In Vitro Evaluation ◽  
Metal Free ◽  
Sequential Transformation ◽  
High Yields

Herein, we design and synthesize an array of benzofuro[3,2-c]quinolines starting from 3-(2-methoxyphenyl)quinolin-4(1H)ones via a sequential chlorination/demethylation, intramolecular cyclization pathway. This sequential transformation was efficient, conducted under metal-free and mild reaction conditions, and yielded corresponding benzofuro[3,2-c]quinolines in high yields. In vitro biological evaluation indicated that such type of compounds showed excellent antileukemia activity and selectivity, and therefore may offer a promising hit compound for developing antileukemia compounds.

scholarly journals Direct access to multi-functionalized benzenes via [4 + 2] annulation of α-cyano-β-methylenones and α,β-unsaturated aldehydes

RSC Advances ◽  
2020 ◽  
Vol 10 (49) ◽  
pp. 29171-29174 ◽  
Author(s):  
Qianfa Jia ◽  
Yunfei Lan ◽  
Xin Ye ◽  
Yinhe Lin ◽  
Qiao Ren
Keyword(s):  
Direct Access ◽  
Reaction Conditions ◽  
Metal Free ◽  
Unsaturated Aldehydes ◽  
Wide Range ◽  
High Yields

An efficient [4 + 2] benzannulation of α-cyano-β-methylenones and α,β-unsaturated aldehydes was achieved under metal-free reaction conditions selectively delivering a wide range of polyfunctional benzenes in high yields respectively (up to 94% yield).

scholarly journals Synthesis of depsipeptides via isocyanide-based consecutive Bargellini/Passerini multicomponent reactions

SynOpen ◽  
2021 ◽  
Author(s):  
Hassan Farhid ◽  
Mohammad Mahdi Rostami ◽  
Ahmad Shaabani ◽  
Behrouz Notash
Keyword(s):  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Flexible Structures ◽  
Amide Bond ◽  
Environmentally Benign ◽  
Reaction Products ◽  
Reaction Conditions ◽  
New Class ◽  
High Yields ◽  
Straightforward Approach

An efficient and straightforward approach has been established for the preparation of new class of depsipeptide structures via isocyanide-based consecutive Bargellini/Passerini multicomponent reactions. 3-Carboxamido-isobutyric acids bearing an amide bond were supplied via Bargellini multicomponent reaction from isocyanides, acetone, and chloroform in the presence of sodium hydroxide. Next, via the Passerini multicomponent reaction strategy, a new class of depsipeptides was synthesized using the Bargellini reaction products, isocyanides, and aldehydes under environmentally benign reaction conditions. The prepared depsipeptides have more flexible structures than their pseudopeptidic analogs. Using cheap and readily available starting materials, mild reaction conditions, simple procedures, and high yields are the advantages of the present strategy.

Transition-Metal-Free Synthesis of Trifluoromethylated Furans via a Bu3P-Mediated Tandem Acylation–Wittig Reaction

Synlett ◽  
2020 ◽  
Vol 31 (20) ◽  
pp. 2035-2038
Author(s):  
Wei Zhou ◽  
Maizhan Li
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Nucleophilic Addition ◽  
Wittig Reaction ◽  
Reaction Conditions ◽  
Metal Free ◽  
Highly Efficient ◽  
Intramolecular Wittig Reaction ◽  
High Yields

AbstractA highly efficient nucleophilic addition–O-acylation–intramolecular Wittig reaction of β-trifluoromethyl α,β-enones is disclosed. This strategy features mild reaction conditions and provides a practical transition-metal-free method to a set of biologically significant trifluoromethylated furans in high yields with diverse functional groups.

A Metal-Free Approach for the Synthesis of 2-Tetralones via Carbanion-Induced Ring Transformation of 2H-Pyran-2-ones

Synthesis ◽  
2018 ◽  
Vol 50 (17) ◽  
pp. 3540-3548 ◽  
Author(s):  
Fateh Singh ◽  
Samata Shetgaonkar
Keyword(s):  
Functional Groups ◽  
Ring Transformation ◽  
Organometallic Reagents ◽  
Metal Free ◽  
Wide Range ◽  
Ultrasound Assisted ◽  
High Yields ◽  
Subsequent Acid

A metal-free, ultrasound-assisted approach for the synthesis of highly functionalized 2-tetralones in high yields is described. The process involves ring transformation of 2H-pyran-2-ones with the spirocyclic ketone 1,4-cyclohexandione monoethylene ketal to yield spiro­cyclic ketals and subsequent acid-mediated hydrolysis. This protocol is free from any organometallic reagents, is economical and tolerates a wide range of functional groups.

Visible-Light-Driven Phosphonoalkylation of Alkenes

Synlett ◽  
2021 ◽  
Vol 32 (04) ◽  
pp. 378-382
Author(s):  
Yue-Ming Jiang ◽  
Jie Liu ◽  
Qiang Fu ◽  
Yu-Ming Yu ◽  
Da-Gang Yu
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Functional Group ◽  
Reaction Conditions ◽  
Metal Free ◽  
Alkyl Sulfonates ◽  
Visible Light Driven ◽  
High Yields

AbstractPhosphonylation of alkenes is important for the generation of valuable organophosphines. However, redox-neutral difunctionalization of alkenes with readily available H-P(O) compounds remains underdeveloped. Herein, we report the first visible-light-driven redox-neutral phosphonoalkylation of alkenes. A variety of organophosphorus-containing three-membered carbocyclic scaffolds are synthesized from alkene-bearing alkyl sulfonates with H-P(O) compounds. The transition-metal-free protocol displays good functional group tolerance, broad substrate scope, high yields, and mild reaction conditions.

scholarly journals Iodide/H2O2 Catalyzed Intramolecular Oxidative Amination for the Synthesis of 3,2′-Pyrrolidinyl Spirooxindoles

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2265 ◽  
Author(s):  
Yu-Ting Gao ◽  
Xiao-Yang Jin ◽  
Qi Liu ◽  
An-Di Liu ◽  
Liang Cheng ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Ammonium Iodide ◽  
Reaction Conditions ◽  
Oxidative Amination ◽  
Metal Free ◽  
High Yields

An ammonium iodide/hydrogen peroxide-mediated intramolecular oxidative amination of 3-aminoalkyl-2-oxindoles was achieved, affording the corresponding 3,2′-pyrrolidinyl spirooxindoles and their 6- or 7-membered analogous in moderate to high yields. This metal-free procedure features very mild reaction conditions, non-toxicity and easily handled hydrogen peroxide as a clean oxidant.

Transition-Metal-Free Synthesis of Thiosulfonates through Radical Coupling Reaction

Synlett ◽  
2018 ◽  
Vol 29 (15) ◽  
pp. 2076-2080 ◽  
Author(s):  
Wen-Ting Wei ◽  
Zhiyong Guo ◽  
Guodong Zhou ◽  
Xu-Dong Xu ◽  
Gan-Ping Chen
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Coupling Process ◽  
Metal Free ◽  
Radical Coupling ◽  
Radical Coupling Reaction ◽  
High Yields

An efficient and practical transition-metal-free radical ­coupling reaction of sulfonyl hydrazides mediated by NIS/K2S2O8 has been developed to afford a variety of biological activity thiosulfonates in moderate to excellent yields. Compared to a known approach for the synthesis of thiosulfonates from sulfonyl hydrazides, this strategy features high yields, mild reaction conditions, and broad substrate scope. The mechanistic studies revealed that the procedure undergoes via a radical cross-coupling process for the construction of S–S bonds.

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